Category: ethers-buliding-blocks

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Development of a validated RP-HPLC method for separation and determination of process-related impurities of omeprazole in bulk drugs》. Authors are Iuga, Cristina; Bojita, Marius; Leucuta, Sorin E..The article about the compound:5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazolecas:73590-85-9,SMILESS:CC1=CN=C(CSC2=NC3=CC(OC)=CC=C3N2)C(C)=C1OC).Reference of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole. Through the article, more information about this compound (cas:73590-85-9) is conveyed.

A gradient reversed phase liquid chromatog. (RP-LC) method was developed and subsequently validated for the determination of omeprazole and its process-related impurities (noted as: impurity A, B, C, D, G, H). Separation was achieved with a Zorbax Extend C18 column and acetonitrile: water: triethylaminel percent (pH adjusted to 9.5) as eluent, at a flow rate of 0.8 mL/min. UV detection was performed at 280 nm. The described method was linear over a range of 40.6-203 μg/mL for omeprazole, 0.9556-14.334 μg/mL for impurity A, 1.1568-17.352 μg/mL for impurity B, 1.0772-16.158 μg/mL for impurity C, 1.289-19.344 μg/mL for impurity D, and 0.7968-11.952 μg/mL for impurity H. The accuracy of the method was demonstrated at 5 concentration levels in the range of 60-140% of the specification limit and the recovery of impurities was found to be in the range of 90-109%. The method is simple, rapid, selective, accurate, and useful for indicating the stability of omeprazole from dosage forms. The method can be useful in the quality control of bulk manufacturing and pharmaceutical formulations.

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Ether – Wikipedia,
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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Validation Study, Journal of Pharmaceutical and Biomedical Analysis called Direct HPLC enantioseparation of omeprazole and its chiral impurities: Application to the determination of enantiomeric purity of esomeprazole magnesium trihydrate, Author is Zanitti, Leo; Ferretti, Rosella; Gallinella, Bruno; La Torre, Francesco; Sanna, Maria Luisa; Mosca, Antonina; Cirilli, Roberto, which mentions a compound: 73590-85-9, SMILESS is CC1=CN=C(CSC2=NC3=CC(OC)=CC=C3N2)C(C)=C1OC, Molecular C17H19N3O2S, Synthetic Route of C17H19N3O2S.

Anal. and semipreparative high-performance liquid chromatog. (HPLC) enantioseparation of the proton-pump inhibitor omeprazole (OME) and its potential organic chiral impurities were accomplished on the immobilized-type Chiralpak IA chiral stationary phase (CSP) under both polar organic and normal-phase conditions. The (S)-enantiomers were isolated with a purity of >99% ee and their absolute configuration was empirically assigned by CD spectroscopy. A chemo- and enantioselective HPLC method was validated to control the enantiomeric purity of the (S)-enantiomer of OME (ESO), an active ingredient contained in drug products, in the presence of chiral and achiral related substances. The precision, linearity and accuracy of the determination of the (R)-impurity as well as the recovery of ESO from a pharmaceutical preparation were determined The proposed method uses the mixture Me tert-butylether (MtBE)-Et acetate (EA)-EtOH (EtOH)-diethylamine (DEA) 60:40:5:0.1 (volume/volume/volume/volume) as a mobile phase. In these conditions, linearity over the concentration range 0.5-25 μg/mL for (R)-enantiomer was obtained. The limits of detection and quantification were 99 and 333 ng/mL, resp. The intra and inter-day assay precision was <2% (RSD%). As far as I know, this compound(73590-85-9)Synthetic Route of C17H19N3O2S can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Simultaneous determination of omeprazole and their main metabolites in human urine samples by capillary electrophoresis using electrospray ionization-mass spectrometry detection. Author is Nevado, Juan Jose Berzas; Penalvo, Gregorio Castaneda; Dorado, Rosa Maria Rodriguez; Robledo, Virginia Rodriguez.

The authors report a novel method for the simultaneous determination of omeprazole and their main metabolites (omeprazole sulfide, omeprazole sulfone and 5-hydroxy omeprazole) in human urine samples. For this purpose, two new capillary electrophoresis (CE) methods were developed for the simultaneous determination of target compounds, using initially diode-array for optical detection and electrospray ionization-mass spectrometry (ESI-MS) for metabolites identification and identity confirmation. A new metabolite (5-hydroxysulfide omeprazole) was identified by electrospray ionization multi-stage mass spectrometry (ESI-MS2) fragment which was then used to support the proposed chem. structure. Pharmacokinetic results using CE method were compared with those obtained when a HPLC method was used. Equivalent pharmacokinetics profiles resulted when any anal. methods were carried out.

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Ether – Wikipedia,
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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called A novel class of ethacrynic acid derivatives as promising drug-like potent generation of anticancer agents with established mechanism of action, published in 2016-10-21, which mentions a compound: 56621-48-8, mainly applied to ethacrynate derivative preparation antitumor antiproliferative structure activity glutathione transferase; Anticancer agents; Ethacrynic acid; Ethacrynic acid derivatives; Glutathione S-Transferase π, Recommanded Product: 4-(Piperazin-1-yl)phenol.

The well-known diuretic Ethacrynic acid (EA, Edecrin), showing low anti-proliferative activities, was chem. modified at different positions. The new EA derivatives have been tested in vitro in anti-proliferative assays on both tumor KB (epidermal carcinoma) and leukemia HL60 (promyelocytic) cells suitable targets for anticancer activity. Reduction of the α-β double bond of EA completely abolished anti-cancer activities, whereas introduction of either 2-(4-substituted phenyl)ethanamine (series A) or 4-(4-substituted phenyl)piperazine (series B) moieties generated compounds showing moderate to strong anti-proliferative activities against human cancer cell lines. Several substitutions on the Ph of these two moieties are tolerated. The mechanism of action of the EA derivatives prepared in this study is more complex than the inhibition of glutathione S-transferase π ascribed as unique effect to EA and might help to overcome tumor resistances.

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Reference:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Journal of Labelled Compounds and Radiopharmaceuticals called Synthesis of novel WAY 100635 derivatives containing a norbornene group and radiofluorination of [18F]AH1.MZ as a serotonin 5-HT1A receptor antagonist for molecular imaging, Author is Herth, Matthias M.; Kramer, Vasko; Roesch, Frank, which mentions a compound: 56621-48-8, SMILESS is OC1=CC=C(N2CCNCC2)C=C1, Molecular C10H14N2O, Product Details of 56621-48-8.

5-HT1A receptors are involved in a variety of psychiatric disorders and in vivo mol. imaging of the 5-HT1A status represents an important approach to analyze and treat these disorders. We report herein the synthesis of three new fluoroethylated 5-HT1A ligands (AH1.MZ, AH2.MZ and AH3.MZ) as arylpiperazine derivatives containing a norbornene group. AH1.MZ (Ki = 4.2 nM) and AH2.MZ (Ki = 30 nM) showed reasonable in vitro affinities to the 5-HT1A receptor, whereas AH3.MZ appeared to be non-affine toward the 5-HT1A receptor. The receptor profile of AH1.MZ and AH2.MZ showed selectivity within the 5-HT system. 18F-labeling via [18F]FETos to [18F]AH1.MZ was carried out in radiochem. yields of > 70%. The final formulation of injectable solutions including [18F]FETos synthon synthesis, radiosynthesis and semipreparative high-performance liquid chromatog. (HPLC) separation took no longer than 130 min and provided [18F]AH1.MZ with a purity of >98% as indicated by anal. HPLC analyses.

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Reference:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 4-(Piperazin-1-yl)phenol. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 4-(Piperazin-1-yl)phenol, is researched, Molecular C10H14N2O, CAS is 56621-48-8, about Novel N,S- and S,S-substituted dienes synthesized from mercapto triazole and some amine derivatives. Author is Ibis, Cemil; Aydinli, Goeksin.

2-Nitro diene Cl2C:CClC(NO2):CCl2 reacted with 3-mercapto-1,2,4-triazole (I) and cyclohexanethiol to yield the resp. dithioacetals Cl2C:CClC(NO2):C(SR)R1 (II; R = 1,2,4-triazol-3-yl, cyclohexyl; R1 = SR). Dithioacetals II (R = 1,2,4-triazol-3-yl; R1 = octylthio, decylthio, hexdecylthio, cyclohexylthio) were obtained by reactions of appropriate vinyl sulfides with I. Novel N,S-substituted dienes were obtained by treatment of II [R = decyl, R1 = Cl (III)] with piperazines. Compound III was reacted with N-(2-aminoethyl)morpholine to give the corresponding N,S-substituted diene. Compound III gave a new N-butadienylhomopiperazine on reaction with homopiperazine in CH2Cl2. Compound II (R = cyclohexyl, R1 = cyclohexylthio) was characterized by single-crystal x-ray diffraction [monoclinic, space group P21/n, a 12.0862(12), b 11.1625(8), c 16.337(1) Å, β 110.840(4)°, V 2059.9(3) Å3, Z 4].

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Reference:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole, is researched, Molecular C17H19N3O2S, CAS is 73590-85-9, about Oxygen dependence of omeprazole clearance and sulfone and sulfide metabolite formation in the isolated perfused rat liver.Safety of 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]thio]benzimidazole.

This study, in the isolated perfused rat liver, examined the O dependence of the hepatic elimination of omeprazole, a drug which undergoes extensive oxidative metabolism in the rat. The relationship between hepatic O supply and the production of omeprazole’s oxidative sulfone and reductive sulfide metabolites was also examined Rat livers were perfused with a perfusate containing 5 μg omeprazole/mL in a single-pass design. Omeprazole clearance and the formation clearance of the 2 metabolites were measured in each liver during normal oxygenation, at different levels of hypoxia and after reoxygenation. There was a linear relationship between omeprazole clearance and O delivery over the whole range studied. Production of the sulfone was similarly O-dependent whereas the sulfide was detectable only after a significant reduction in oxygenation. In further experiments the O dependence of omeprazole clearance was not altered when the concentration of drug was lowered to 1 μg/mL. This study shows that O delivery is a critical determinant of the rate of oxidative drug metabolism in the isolated liver and supports the contention that reductions in hepatic O supply may alter the hepatic disposition of oxidatively metabolized drugs in vivo.

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Category: ethers-buliding-blocks. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-(Piperazin-1-yl)phenol, is researched, Molecular C10H14N2O, CAS is 56621-48-8, about Different nematic phases and a switchable SmCP phase formed by homologues of a new class of asymmetric bent-core mesogens.

Ten homologues of a class of asym. bent-shaped liquid crystal compounds were synthesized by reaction of 4-(4-alkyloxy-benzoyloxy)benzoyl chlorides with N-(4-hydroxyphenyl)piperazine. The mesophase structure and transitions of the compounds were studied by polarizing microscopy, x-ray diffraction, dielec. and electro-optical measurements. The long-chain members of the series C8-C16 exhibit the switchable polar antiferroelec. smectic phase ( SmCP). The short-chain members, C4-C8, form a nematic phase. The homologues C5 and C6 show a transition from nematic to a low-temperature phase which is indicated by a sharp peak in the DSC trace. Whereas the texture of the phase points to a nematic-smectic transition, the x-ray studies definitely prove a structure without any long range (or quasi long range) positional order in the low-temperature phase. A mol. model is described which exhibits structural features similar to those of a nematic phase, which can be regarded as the precursor of the following columnar phase (B1 phase).

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Ether – Wikipedia,
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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called An efficient asymmetric approach to the R-enantiomer impurity of esomeprazole, published in 2016, which mentions a compound: 73590-85-9, mainly applied to esomeprazole preparation enantioselective, HPLC of Formula: 73590-85-9.

The R-enantiomer of esomeprazole (5-methoxy-2-[(4-methoxy-3, 5-dimethyl-2-pyridinylmethyl)sulfinyl]-1H-benzimidazole) was synthesized with high enantioselectivity by asym. oxidation of prochiral sulfide using the oxaziridinium salt. This (R)-enantiomer, useful as a reference for the quality control of esomeprazole was characterized by 1H and 13CNMR, IR and HRMS. The enantiomeric excess was determined by HPLC.

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Ether – Wikipedia,
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Li, Bing-Yu; Voets, Lauren; Van Lommel, Ruben; Hoppenbrouwers, Fien; Alonso, Mercedes; Verhelst, Steven H. L.; De Borggraeve, Wim M.; Demaerel, Joachim published the article 《SuFEx-enabled, chemoselective synthesis of triflates, triflamides and triflimidates》. Keywords: triflate triflamide triflimidate synthesis click reaction.They researched the compound: 4-(Piperazin-1-yl)phenol( cas:56621-48-8 ).Reference of 4-(Piperazin-1-yl)phenol. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:56621-48-8) here.

Sulfur(VI) Fluoride Exchange (SuFEx) chem. has emerged as a next-generation click reaction, designed to assemble functional mols. quickly and modularly. Here, we report the ex situ generation of trifluoromethanesulfonyl fluoride (CF3SO2F) gas in a two chamber system, and its use as a new SuFEx handle to efficiently synthesize triflates and triflamides. This broadly tolerated protocol lends itself to peptide modification or to telescoping into coupling reactions. Moreover, redesigning the SVI-F connector with a S=O → S=NR replacement, furnished the analogous triflimidoyl fluorides as SuFEx electrophiles, which were engaged in the synthesis of rarely reported triflimidate esters. Notably, experiments showed H2O to be the key towards achieving chemoselective trifluoromethanesulfonation of phenols vs. amine groups, a phenomenon best explained-using ab initio metadynamics simulations-by a hydrogen bonded termol. transition state for the CF3SO2F triflylation of amines.

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Ether – Wikipedia,
Ether | (C2H5)2O – PubChem